Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Reexamination Certificate
2002-05-13
2004-04-06
McKane, Joseph K. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
C558S147000
Reexamination Certificate
active
06717005
ABSTRACT:
BACKGROUND OF THE INVENTION
It is known to add epoxy compounds as stabilizers to monophosphate compounds that find utility as functional fluids. Examples of patents describing such an approach include: U.S. Pat. Nos. 3,637,507 to W. F. Gentit; 3,932,294 to M. L. Burrous; and 3,941,708 to W. F. Gentit et al.
A class of distinctly differing polyphosphate compound is also known that has the formula:
where n, on a number average basis, ranges from about 1 to about 5 R is aryl, such as phenyl, or alkaryl, and R′ is arylene (such as derived from resorcinol), arylene-alkylene-arylene (such as derived from bisphenol A), or alkylene (such as neopentylene). These polyphosphate esters are used, for example, as flame retardants and plasticizers for plastics and are prone to hydrolysis that produce phosphoric acids that are undesirable degradation products. These acid species can cause decomposition of polycarbonate resins.
Various approaches are described to solve the afore-mentioned problems of degradation. European Patent No. 909,790 to General Electric Company describes the addition of an acid scavenger, such as an epoxy compound, to a composition comprising the polyphosphate and the resin. In U.S. Pat. No. 5,871,570 to T. Koyama a similar approach is advocated where an epoxy compound not containing halogen is added to a polycarbonate resin composition containing an organic phosphorus-type flame retardant and other additives. Japanese Published Patent Application No. 2001/2945 describes adding an alicyclic epoxy compound to a resin composition that also contains an organic phosphorus flame retardant. In this general approach the epoxy compound is added to the polyphosphate only after it has been to the resin system that it is intended to also contain the flame retardant.
Another approach has been to add the epoxy compound to the polyphosphate at some point in its manufacturing process after it has been formed. PCT Published Patent Application No. 2001/12638 to Daihachi describes treating the phosphate compound with epoxy and then with an aqueous alkali solution. U.S. Pat. No. 5,616,768 to S. Kawata treats a crude phosphate product with an epoxy compound, heats the resulting product in the presence of water, washes the product with water, and removes the residual water. Japanese Published Patent Application No. 2001/151,786 describes an aromatic polyphosphate composition that is stabilized by the addition of bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite and 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate.
Japanese Patent Publication No. 2001/131,392 (May 15, 2001) illustrates a flame retardant composition that comprises an organophosphorus compound and an epoxy compound having an acid number of 1 or less.
DESCRIPTION OF THE INVENTION
This invention relates to such polyphosphate compositions that have been stabilized by the addition of a certain class of epoxy stabilizer. This invention allows for a polyphosphate/epoxy stabilizer pre-mix that can thereafter be added to a substrate resin (e.g., an engineering resin) to stabilize the final flame retarded resin formulation.
The epoxy stabilizer of choice herein is one or more cycloaliphatic epoxy compounds having a C
6
to C
20
cycloaliphatic ring. They are alicyclic epoxy compounds where the alicyclic epoxy structural units are linked through a bonding unit, which is either a dioxane, or a carboxyl structural unit. Useful cycloaliphatic epoxy compounds include: 3,4 epoxycyclohexylmethyl 3,4 epoxycyclohexane carboxylate, which is available as ERL-4221 (a Union Carbide Corporation trademark) and ARALDITE CY-179 (a Ciba-Geigy trademark); the diglycidyl ester of hexahydrophthalic anhydride, which is available as CY-184 (a Ciba-Geigy trademark); bis(3,4-epoxycyclohexylmethyl)adipate, which is available as ERL-4299 (a Union Carbide trademark), vinyl cyclohexene dioxide (ERL-4206), vinyl cyclohexene monoxide, and 2-[3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy]-cyclohexane-meta-dioxane (ERL-4234]. In general, this epoxy component can be selected from the cycloaliphatic epoxides (including diepoxides). Examples of such structures are shown below:
The addition of 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate (ERL 4221 from Union Carbide) to these polyphosphate esters is preferred and prevents the formation of acidic species under conditions of high temperature and humidity and gives polyphosphate esters of high hydrolytic stability which can then be added, if desired, to resins to stabilize the resulting resin.
In general terms, the amount of epoxy to use will range from about 0.01% to about 1%, by weight of the polyphosphate composition. The admixture of polyphosphate and epoxy additive are advantageously allowed to stand at a temperature of from above about room temperature to 150° C. for periods of time ranging from about eight hours to about fifteen minutes, respectively.
The stabilized polyphosphate compositions of this invention, when treated with water at 90° C. for thirty-five days, for example, do not show an increase in acidity thus demonstrating their attractive hydrolytic stability characteristics. The present invention will be further understood by the Examples that follow.
REFERENCES:
patent: 3637507 (1972-01-01), Gentit
patent: 3932294 (1976-01-01), Burrous
patent: 3941708 (1976-03-01), Gentit et al.
patent: 4696963 (1987-09-01), Albright et al.
patent: 4992496 (1991-02-01), Green
patent: 5464551 (1995-11-01), Deetman
patent: 5616768 (1997-04-01), Kawata et al.
patent: 5871570 (1999-02-01), Koyama et al.
patent: 909790 (1999-04-01), None
patent: 2001-002945 (2001-01-01), None
patent: 2001/-131392 (2001-05-01), None
patent: 2001-151786 (2001-06-01), None
patent: 01/85881 (2001-11-01), None
CA Plus Abstract of Japanese Patent No. 2001-151786.
Derwent Abstract 2001-218340/22 (2001).
Derwent Abstract 2001-260398/27 (2001).
Bright Danielle A.
Buczek Mark
Burkhardt Eric W.
Dashevsky Sophia
Levchik Sergei
Akzo Nobel N.V.
Fennelly Richard P.
McKane Joseph K.
Saeed Kamal
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